GB2201415A - Ferroelectric liquid crystals - Google Patents

Ferroelectric liquid crystals Download PDF

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GB2201415A
GB2201415A GB08802977A GB8802977A GB2201415A GB 2201415 A GB2201415 A GB 2201415A GB 08802977 A GB08802977 A GB 08802977A GB 8802977 A GB8802977 A GB 8802977A GB 2201415 A GB2201415 A GB 2201415A
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mol
mixture
ferroelectric liquid
chlor
methyl
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GB2201415B (en
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Bak Gun Yong
Petra Barth
Dietrich Demus
Detlev Joachimi
Barbara Kampa
Kristina Mohr
Reinhard Paschke
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Werk Fernsehelektronik Veb
Werk fuer Fernsehelektronik GmbH
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Werk fuer Fernsehelektronik GmbH
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    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/16—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms condensed with carbocyclic rings or ring systems
    • C07D249/18—Benzotriazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D277/36—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
    • C07D285/01—Five-membered rings
    • C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
    • C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
    • C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
    • C09K19/12—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings at least two benzene rings directly linked, e.g. biphenyls
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
    • C09K19/20—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers
    • C09K19/2007—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers the chain containing -COO- or -OCO- groups
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
    • C09K19/3441—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/42—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40

Description

1 1 1 1 1 1 I T', 2'201415 Ferroelectric liquid crvstalJ, This invention
relates to ferroelectric liquid crystals for the production of rapid switching displays having storage properties for the display of digits, symbols and images.
It is known to use ferroelectric liquid crystals for the production oL rapid switching displays having storage properties (N.A. Clark, S. TLagerwall, Appl. Phys. Lett..16, 899 (1980)).
The number of ferroelectric liquid crystal compounds has greatly increased in recent times, but there are still no pure substances possessing optimum properties-(S.T. Lagerwall, J. Wahl, N.A. Clark, Proceed. SID Symposium October 1985 San Diego USA; J.N. Goodby Science 231, 350 (1986), F. Dahl, S.T. Lagerwall, Ferroelectrics 58, 215 (1984), D. Demus, 1H. Zaschke, Fltssige Kristalle in Tabellen ("Liquid Crystals in Tables") II, Leipzig 1984).
Many ferroelectric liquid crystals are chemically and thermally not very stable, possess high melting temperatures or their spontaneous polarization is not sufficient. On account of the too small dipole moments andthe associated low spontaneous polarization, the derivatives of-the 2-methyl-butyl group and other chiral-branched alkyl chainsare unsuitable for practical use as a consequence of their too long switching, times.
01 1 Other ferroelectric liquid cli-ystals contain the azomethin grouping and as Schiff bases are not very stable against heat, moisture and acids. Some ferroelectric liquid crystals derived from chiral CL-chlorio carboxylib acids (J.-K. Goodby _et al, Proceed. of 1983 A.C.S. Meeting Las Vegas, Nevada 1982. Liquid Crystals and Ordered Fluids Volume 4 F 1) exhibit too high melting temperatures.
01 1 v C The obj.ective of the present invention is rapid switching displays having storage properties, which contain chemically and thermally stable ferroelectric Iiquid erystaliine substances.
The task of the invention is ferroelectric liquid crystals which can be used in rapid switching displays having storage properties.
According to the invention it has been found that compounds which contain a chiral halogen alkyl residue according to general formula I 9R'-CH-(CH) -(CO) -M - (CH) -(0) - ( -(y)n 1 2 a b r 2 c, q ? X (E) d B -(Z) 0 C -R 2 X d (E) d where a = 0,1,2 b, c. d. n, m, o, p, q, r = 0,1 X = Pp Bry Cl Y = -COO-9 -OOC-p -CH 2 -CH 2-' -CH 2---0-1 -0-CH 2_ Z = Y1 -CH 2-1 -N=N-, -N=N(O)- E = halogen, -CN, -CH 3' -NO 21 -OCH 3 01 I N 9-. -, 0 - 0 ' N -W, No' S 0 Xj 00)- -C, ' Y'O' il?- v - ' l- J ' -G)- = -GY-, -(D- = -(5- ' 1 R = c 1 H 21+11 (CH 3)2 CH-, (CH 3)2 CH-CH 2-' c 2 H 5_ CH(CH 3)- 2 R = c k H 2k+l_1 C02k+10-' ek H 2k+lS-1 Ck H 2k+lCO-' c k H 2k+1 COO-, C kH2k+looe-' Ck H 2k+1 NH-9 1 = 3 to 12, k = 1 to 12 and, if n = 0 and -C is only equal to. -G- 1 then can also be a benzene ring; if b = 0, then a must be equal to 1, are ferroelectrically crystalline liquid.
In mixtures with one another and with other liquid crystalline substances or non-crystalline liquid substances, they form ferroelectrical crystalLine I'. quid; phas es; -.tnd ire -.biitalsle, for. uj,,-. n disp.lay,.
I, 1 1 1 p Y The substances are produced according to a method which itself is, known, f or example by esterif ication of. chiral d -halogen carboxylic acids: o. r their derivatives with corresponding hydroxy compounds, according to the following arrangement:
4 - R 1 -CH-(CH 2 a -(CO) b-el X +HO- (CH j (0) (y) 2 q n (E) B - M o c 1 R /P 00 (C 1011b (E) d (E) d I The chiral d -halogen carboxylic aciasare obtained by reaction of commercially obtainable chiral d-amino acids by decomposition of racemates of the C -halogen carboxylic acidsor by asymmetrical synthesis. Other derivatives are produced by esterification with A -halogen -- carboxYlic acids or reaction with other chiral halogen alkyl derivatives.
As a consequence of the high dipole moments of the halogen alkyl derivatives, the substances possess a high spontaneous polarization and thus short switching times in optoelectronic displays.
Exam.ples of embodiment Example 1
In tables 1 and 4, substances that concern the invention are listed.
J P Tables 2 and 3 contain already known substances, which were used as mixture components.
p i g The following meanings are used:
crystalline solid state S c ferroelectric smectic C-phase.
SAYS13 smectic A. B-phase CH cholesterinic phase I N isotropic liquid phase nematic phase unclassified smectic phase 1 The numbers between the phase designations indicate equilibrium temper- atures in 0 C.
IF 1 Table 1 i 'i Nr.1x91 S S, 137 0 196 HCOO- SA CH 3)2 CH-C -OC H 108 X '158 1 \ o Co 6 13 6 13 Nr 2- C,m, - CH-CHe oJ n. N 2;:- - CH 3 cl CH-C.l-COO- H Nr. 3 C0;1 312 % X-d / P4 1021 (. '95) 148 Xl - - 4 - QC14 -, f?. li-c-oc 5 H 11 i IN C 1 i 1 4. N R.r. E; (cm 3)2 CH-CH 2 -CH-COO o l-./ 0 _oc 5 H 11 132 1 \ -/ cl 1 179.
a 159 a 4 172 6 186,5 'i 168 - -CH-CH-t,00-.-# 0 Ok -OC H '153 172 2:'5 v 162 Nr..7 - CH-C-COO OC H. 105 158 (C"3)2 \0 919 1 -00 Nr. 9 <>f ---CHCl-CH 0 C H. 137 138 238(Z) -Coo-( 0\' 10 2 1 2 1 1 Nr. 9a CH3-CHCl-CH 2COO-(:, Nr. 9b Nr. 13c Nr. 9d Nr.. ge 1% Nr gf K CH 3-CHCl -CH 2 COO-D$ oc 6 H 3 13 CR 3 -PHCl-CH 2 COO-C)-COG-00 - oc 6 H 13 63 A.
C1 3 -CHCl-CH 2 COO-/OOC--& C.10H 21 A CH 7CHCl-CH CM-00 'lr---o OC H 3 2 10 21 CH -CHM-6H C()0 o 00 OC H 3 2 8 -17 1 Unclassified smectic phase 1 1 k k S X S c -A C H a 150 (.13) 96 (.
106 0 0 87 0.58 1) 6 66.
95).10,61) 136.154 1) (.1 - I 1 co 1 1 1 Table 2
Nr. 99 (CH 3)2 CH-CH-C00-&C()0-\T/,Yc, H 19 4 cl K 0 A.
Nr. 9h (PH)2 CH-H-CO( 0 ooc oc 9 H 17 3 CL)-&&', - &0 Nr. 10 (CH 3)2 CH-CH-COI (0-Ooc--&Oc 6 H 13 86 cl 4 Nr. 11 (CH 3)2 CHCH-COG-& 00c- & oc a H 17 1 cl Nr. 12 (CH 3)2 CH-CH-COG-&0OC-&OC10H 21 CL 4 r H Nr. 13 (CH 3)2 CH-CH-COG--&OOC-\0C12 25 cl 0 S C.
73 (. 69) 87 154 1 0 132 - --- k 49 0 6 66 (. 45) a 62 (. 42) 1. SA - CH ss - - - 0 68 69 0 f 1 0 157 0 0 lee a - -0 196 A 0 72 BP74. 1 A 0 70SP72 a 9 Table. 3
Nr. 14 C H 17 ocoo- & coo- & C 9 H 19 Nr. 15 CaH 17 0 --&Coo-&OC6H13 Nr..16 C a H 17 0 0 C 9 H 19 - Nr. 17 C H >CgH, 6 13 K S 0 34 S 34 - C A 9 55. 66 33. 565.74#5 - 24. 43 N T - 56 @_ ages 69,5.70,5 9 9 01 Table. 4
K Nr. 18 c 8 H 17 0-1 -coo-G-OOC-CH-CH (Clt) 2 80 cl cl 1 Nr. 19 C H 07( -0OC-CH-CH(CH 3)2 73 : 10 21 COO 1 1. cl cl 1 c rr Nr. 20 C H 0 00- 0 -CH OOC-CH-CH(CH 8 17 c ' 2- 3)2 i cl 1 Nr. ?1 c 10 H 21 0 00 -14 2-OOC-CH-CH(CH 3)2 o -(D-C 1 cl 1 0 41 9 4 Nr. 22 c 8 H 17 0- COO- COO-., 0 -CH OOC-CH-CH(CH 3)2.72 54) \D\n 2 1 0 k_ L 1 0 Nr. 2--R C H -N-C ll C=CH-(_)-OOC-CH-CH(CH 3)2 1 1 / cl C-S S Nr. 24 C H -Al 0 -OCH -CH -OOC-CH-CH(CH 44 2 2 3)2 6 13 \= t4KD q. i cl CH I 118. 124-5.
A N 2 N 0 N-OOC-Y 0 OOC-CH-CH(CH 3)2 142 165 N cl 1 1 1 v c a, 1 1 1 111 1, -F- 0 0 R 1 -4 W-0 Nr. 26 (CH) CH-CH-C-0- & < H 3 2 1 11 > '-T-OC5 j cl 0 A 0- 11 oc 8 H 17 Nr. 27 (CH CH-CH-C - 3)2 1.
cl o N-M 1 K S 1 In c 157,5 0 (157) 0 80 Nr. 28 (CH 3)2 CH-CH-C-0--_>oc 9 H 19 1 1 1 cl 0 N 1 c 10 H 21 0 lx- Nr. 29 (CH 3).-CH-CH, C-O-& cl 0 4 41 111 N is 0 0 167,5. 177 a 0 1067 165,5.
0 168 128. 147,5.148 0 0 F A f 1 9, . 5 Example. 2
From the.substances according to this inventipn in Table 1 and the compounds lis ted in Tables 2 and 3, the following mixtures were produced.
Mixture 1 The mixture. consists of Nr. 9g (S)-5-n-Nonyl-2-(4-(4-(2-chlor-3-methyl-butyryloxy) benzoyloxy)phenyl)-pyrimidine Nr. 14 4-n-'octyloxycarbonyloxy-benzoic acid -(4-n-nonyl- M01-% phenylester) 60 Mol-% Mixture 2 The mixture consists of Nr. 14 4-n-Octyloxycarbonyloxy-benzcLc acid -(4-n-nonylphenylester) Er. 11 (S)-4-n-Octyldxybenzoic acid.- (4-(3-chlor-3-methylbutyryl-oxy)phenylester) Mixiure - 3 -The mixthre-conEists-of Nr. 1 (S)-5-(4-n-Hexyloxy-phenyl)-2-(4-(2-chlor.3-me.t.hylbutyryloxy)phenyl)-pyrimidine Nr. 11 (S)-4-n-Octyloxybenzoic acid -(4-(2-chlor-3-meihyl- butyryloxy)-phenylester) Mixture 4 The 'mixture _consists Nr 11 (S)-4-n-Octylc)xybenzoic acid- -(4-(2-chlor-3-methyl butyryloxy).-phenylester) Nr. 13 -4-r-Ood ecyl.o gybe nme:c, thylbutyry'Loxy)-phenylester) Nr. 3 (S-3-(4-n-')ezyl-phenyl-2-(4-(2-chlor-3-methylbu&byryl.oxyj-,-..'-, eny-l',-py,--4midine Mol-% M01-% Mol-'lo M01-% 73 Mol-% 13 Mol-% 14 Mol-% ,n 1 lz Y 1 Mi-xture 5 The mixture consists of Nro 11 (S)-4-n-Octyloxybenzoic acid -(4-(2-chlor-3-methylbutyryloxy)-phenylester) Nr, 99 (S)-5-n-Non1-2-(4-(4-(2-chlor-3-methylbutyryloxy)-benzoyloxy)-phenyl)-pyrimidine Nr. 15 4-n-Octyloxybenzcic acid -(4-n-hexloxy phenylester) Nr. 14 4-n-Octyloxycarbonyloxy-benzoidacid-(4-n- nonylphenylester) Mixture 6 The mixture c-on&ists of Nri 11 (S)-4-n-Octylo,,lboiizoic acid. -(4-,,,-,-clilor-3-methyl- butyryloxy)-phdnylester Nr. 3 (S)-5-(4-n-Decyl-phenyl)-2-(4-(2-chor-3-meth butyryloxy)-phenyl)pyrimidine Nr. 15 4-n-Octyloxybonzoic acid -(4-n-hexyloxy-phenyl- ster) Nr. 14 4-n Octyloxycarbonyloxy-benzbic acid.-(4-n nonylphenylester) Mixture 7 The mixture consicts of(S)-4-(2-chlor-3-methyl-butyryloxy)-4'(4-n-octyloxybenzbyloxy)-biphenyl Nr. 10 (S)-4-(.2-chlor-3-methyl butyryloxy)-4'-(4-nhexyloxybenzoylogy)-biphenyl Nr. 99 (S)-57n-Nonyl-2-(4-(4-(2-chlor-3-methyl-butyry loxy)-benzoyloxy)-phenyl)-pyrimidine 16 5-n-Nonyl-2-(4-n-octyloxy-phenyl)-pyrimidine Nr.
e 46 Mo 1 -5 M01-5 16 M01-5 23 Mol- 46 Mol-, Mol-',, 16 Mol-, 23 Mol-5 12 Mol-AA 32 Mol- 8 Mol-.
A 48 Mol-5,' 1 k 1 Mixture The mixture consists of (S) -4-(2-Ch l or -3-methyl-butyryloxy)-'-(4-.n-octyloxy-benzoyloxy)- biphenyl Nr. 10 (S)-4 (2-Chlor;3-methyl-butyrylo.y)-4'-(4-n- hexyloxybenzoyl'oxy)-biphenyl Is Mol-% v 49 Mol-% Nre 99 (S)-5-n-Nonyl-2-(4-(4-(2-chlor-i-methyl-butyryloxy)- 1.
behzoyloxy)-phenyl)-oyrimidine 13 Mol-% Nr. 16 5-n-Nonyl-2-(4-noctyloxy-phenyl)-pyrimidine. 20 Mol?-% Mixture..9 The mixture consists of (j)-4-(2-Chlor-3-methyl.-butyryloxy)-4'-(4-n-octyloxybenzoyloxy)-biphenyl Nr. 10 (S)-4-(2-Chlor-3-methyl-butyryloxy)-4'-(4-nhexyloxybenzoyloxy)-biphenyl Nr. 9g (,S)-5-n-Nonyl-2-(4-(4-(2-chlor-3-methyl-butyryloxy)benzoyloxy)phenyl)-pyrimidine Nr. 17 2-(4-n-Hexyloxyphenyl)-5-n-nonyl-pyrimidine Mixture 10.20 The-mixture consists of 18 Mol % 49 Mol-% 13 Mol-% Mol-% (S)-4-(2-Chlor-3-methyl-butyryloxy)-4-(4-n-octyloxy- benzoyloxy)-biphenyl 12 Mol-% Nr, 10 (S)-4-(2-C.hlor-3-methyl-butyryloxy)-4-(4-n-hexyloxybenzoyloxy)-iphenyl 32 Mol-% Nr. 99 (S)-5-n-Nonyl-2-(4-(4"(2-Chlor-3-methyl-butyryloxy)benzoyloxy)phenyl)-pyrimidine Nr. 16 5-n-Nonyl-2-(4-n-octyloxy-phenyl)-pyrimidine Nr. 12. (S)-4-n-Decyloxy-benzoic. acid -(4-(2-Chlor3-methylbutyryloxy)-phenylester) f 8 M91-% Mol-% 28 Mol-% Ii t..
1 il 17 - Mixture 'Of The mixture c-onsists! -'(S) -4- (2-Chlor-3-m c thylbu tyryloxy) -4'- (4-n-oc tyloxy- benzoyloxy)-iphenyl.16 M01;-% Nr. 10 (.S)4-(2-Chlor-3-methyl-butyryloxy)-4'-(4-n-hexyloxy- benzoyloxy)-biphenyl 43 Mol% Nre 99 (S)-5-n-Nonyl-Z-(4-(4- (2'chlor-3-methyl-butyrylox). benzoyoxy)- phenyl)-pyrimidine Nro, 16 5-n-Nonyl-2-(4-n-octyloxy-phenyl)-pyrimtdin Nre 2 (6)-4-n-Decyloxy-benzoic acid-(4-(2-Chlor-3-methyl- butyryloxy)-phenylester) Mixture... 12 The mixtu're 'consists of -10 M01 % MO I'.% 1 11 M01-% 0 (S)-4-(2-ChlOr-3-methyl-butyryloxy)-4'-(4-n..!octyloxybenzoyloxy).-biphenyl 16 M01-% Nr. IQ (S)-4-(2-Chlor-3-methyl-butyryloxy)-4'(4-n-hexyloxyb-enzoyloxy)- biphenyl W..99 (s)-5-n-Nonyl-2-(4-(4-(2-chlor-3-methyl-butyryloxy)benzoyloxy)-phenyl.)-pyrimidine Nr. 17 2-(4-n-Hexyloxy-phenyl)-5-n-nonyl-pyrimidin Nre 12 (S)-4-n-Decyloxy-benzoic aci-&-(4-(2-Chl6r-3methylbutyryloxy)phenylester) These-mixtures- possess the following equilibrium temperatures:
CH 1 c A 1 22s5 2 34 3 36 4 33 16 6 is 7 19 8 44 9 32 30 11 38 12 32 43 Mol- M61-% Ma.1-% 11 M01-% 9.0 0 47 37. 66 5,5 41 35 80 100 100,5 66 91,5 so r 56 110 99 77,5 43 81,5 76 86#5 93 114 108 135 106 191 113 104 129 103 127,5 1 1 1 4 Th e following examples provide production methods for the compounds according io this invention.
Example 3
Production of (S)-2-(4-(2-Chlor-3-methyl-butyryloxy)-phenyl)-5(4hexyloxyphenyl)-pyrimidin6 (No. 1) A. 2-(4-b:ydroxyphenyl)-5-(4-hexyloxy-phenyl)-pyrimidine 0.01 mol of 4-bydroxybenzamidine-hydrochloride and 0.01 mol of 3dimethylamino-2-(4-hexyloxyphen yl)-N,N-dimethyl propene (2)immoniumperchlorate are heated in 100 ml of triethylamine for 8 hours with reflux. After cooling, th e mixture is poured onto icelconcentrated H 2 so 4 (200 g:25 ml), and the precipitate is sucked off and recrystalized several times from methanol.
Yield: 2.6 g (75% of theoretical value) F: 155 0 C - B. (S)2-(4-(2-Chlor-3-methyl-butyryloxy)-phenyl)-5-(4hexyloxyphenyl)pyrimidinfa To a solution of 0.005 mol 2-(4-hydroxyphenyl)-5-(4- hexyloxyphenyl)pyrimidine, 0.6 mI, CL-iethylamine and 50 mI, absolute tolueneg 0.77 910.005 mol. of (S)-2-Chloro-3-methylbutyryl chloride are added. (The acidic chloride was produced by the known method f:bom the optically active amino acids)._ 0 1 -b 7 1.
The mixture is allowed to stELd for one day at room temperature and is then heated'for one hour at 80 0 C on a water bath. After filtering off of the precipitate, the solvent is distilled out and the residue is recrystallized several times from ethanol.
The yields are 60-70 % of the theoretical value.
Thh liquid crystalline melt behaviour is given in the tables.
Example 4
A. Production of (S)-(+)-3-hydroxy butane acid ethyl ester g of fresh bakers'yeast are slurried with a 300C hot solution of 300 g saccharose in 1.6 litre fresh water and lightly stirred at 300C. After one hour, 0.15 mol of distilled acetoacetic ester are added with thorough stirring and the mixture is lightly stirred for 24 hours at 25-300C. A 350C hot solution of 200 g saccharose in 1 litre of water is then added by portions and, after one hour of thorough stirring, 0.15 mol of aceto acetic ester are again added. The mixture is stirred for 50 hours at 2-5- 300C. Sucking-off over kieselguhr is then carried out and the residue is washed twice with 100 ml water each time. Thepurified aqueous phases are saturated with Na.01 and extracted fivp times with 500 ml ether each time. After separation and drying of the organic phase over Na 2 so 4' the product is concentrated on the rotary evaporator to 50-80 ml. Practionated distillation of the residue provides (S)-(+)-3-hydrbxy butane acid ethyl ester with a yield of 65-75% of theoretical value.
ee = 84 % Kp = 73 0 C 25 = +36.20 12 D 01 (CHCl 3; C = 1.3) 1 B. Production of (R)-(-)-3-chlorobutane acid ethyl ester 0.07 mol of water-free ZnC1 2 are added to 0.24 mol of (S)-(+)-3-hydroxy butane acid ethyl ester in 100 ml benzene with stirring and exclusion of moisture, 0.72 mol of SOC1 2 are then added and stirred at room temperature for 2 days. The reaction mixture is then treated with saturated NaHCO 3 solution. After separation of the aqueous phase, drying is carried out with Na 2 so 4'- the solvent is distilled off and the residue is subjected to fractionated distillation. (R)-(-)-3-chlorobutane acid ethyl ester is obtained in a yield of 65%.- K P16 ' 68 0 c C. Production of (R)-(-)-3-chlorobutyryl (d) D 25 - -14.360 (CHCl 3; C = 4.7) chloride 0.07 mol of (R)-(-)-3-chlorobutyrid acid ethyl ester are thoroughly stirred with 100 ml of concentrated hydrochloric acid until a clear solution is obtained and are then kept for 3 days at 37-40 0 C with light stirring. Dilution is then carried out with 100 ml water, followed by saturation with NaCl and extraction three times with 100 ml ether each time. After drying of the organic phase with Na SO the 2 4' solvent is removed on the rotary evaporator and the residue subjected to fractionated distillation in vaculm. The yield of (R)-(-)-3-chlorobutane acid is 70-75% of theoretical value.
Kp 30 ' 1250C G'U ro'- Of' SOC2. 2 are addtd tLo 0.04 nol (R)-(-)-3-chl-oro-b-atane acid and left to standfor 24 hours at room temperature with exclusion of moisture. The temperature of the mixture is then kept for 11 hours 11 1 ZII 1 1 1.1 - 21 1 at 420C and the mixture is t, Ren subjected to fractionated distillation using an ice-cooled vessel.
Yield: 70-75% of theoretical value KP15 - 450C (d)D 25 - -13.70 (CE01 - C = 7.34) 3, D. Esterification of (R)-(-)-3-chlorobutyryl chloride with phenols and alcohols -3 In a.50 ml Erlenmeyer flask with CaCl 2 tube. 1.7 X 10 mol of the relevant alcohol or phenol are placed in 15-30 ml of THP. After cooling of the solution to -30 0 Cv 2.13 X 10-3 mol (R)-(-)-3-chlorobutyryl chloride and 1.7 X 10-3 mol pyridine are added in succession with stirring. After stirring has been carried out for 10 minutes at -30 0 C. the reaction mixture Is left to stand for 2 days at -20 OG. The mixture is then added to 300 ml of ice-cold 5% hydrochloric acid.
If the ester precipitates out, suction-off is carried out and recrystallization is carried out from iethanol, hexane or benzene.
If the eater does not crystallize In the 5% hydrochloric acid solution. extraction with ether Is carried out three times, followed by drying with Na 2 so 4 and subsequent distillation. The yield of the corresponding esters is 30-70% of the theoretical value.
01 1 A 1

Claims (3)

Claims
1.. Ferroelectric liquid crystalline compounds which contain a chiral Ih.alogen alkyl residue, according to the general formula I J_ R I- CH-(CH (CH 2)a_(C0)b_(0)r_ 2)c_(O)q - \.1 A - (y) n_ X - 1 2 \ 8 (Z) C LR 0 E) d (r--) where K= 0,1,2 b,c,d n m,o p q r 0, L X = F, Br, Cl Y = -COO-, -C)OC-, -CH.-CH -1 -CH2-0-1 -0-CH 2 Z = Y, -CH 2-1 -N=N-, -N=N(O)- E = Halogen, - /\ --A,) - I 2 -CNI, -CH 3' -NO 2' - OCII 3 IV - ti\ /--7) 0 0 n OD - C 1\ Iv 0 N q Q 0 -, - N N h n:_ Y1 E03 r-l E3 0)-,' -UH - C H (CH 3)2 CH-., (CH 3)2 'H-CH 2- CH 1 2!tl' - r- 5 - f 4 C0;)-1 1 c j 1 2 R-. CkH2k+1-1 C02k+1 0-1 Ck H 2k+IS-1 Ck H 2k+IC 0-1 c k H2k+l C00-6 c k H2k+l ooc-, c k H 2k+l NH-, 3 to 12, 1- to 12 and, if n 0 and is aily equal to then can-also be a benzene ring if.bmO, then -a niist be equal to 1.
2. Ferroelectric liquid crystalline mixtures for displays, containing compounds of Formula I according to Claim. 1.
3. Ferroelectric liquid crystalline compound as.claimed in Clairn 1, substantia lly as described in any of the examples disclosed herein.
F Published 1988 at The Patent Office, State House, 68/71 High Holbom London WClR 4TP. Further copies may be obtained from The Patent ofnee, Sales Branch, St Mary Cray, Orpington, Kent BR5 3RD. Printed by Multiplex techniques ltd, St Mary Cray, Kent. Con. 1/87.
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FR2611212B1 (en) 1994-10-14

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